4-Methoxybenzenesulfonyl chloride → Methyl 3-(4-methoxy-benzenesulfonylamino)-2,6-dimethoxy-isonicotinate

HRID 1275587Notes

Reaction equation

HRID 1275587 reaction equation
[NH2:1][C:2]1[C:11]([O:12][CH3:13])=[N:10][C:9]([O:14][CH3:15])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>N1C=CC=CC=1>[CH3:16][O:17][C:18]1[CH:19]=[CH:20][C:21]([S:24]([NH:1][C:2]2[C:11]([O:12][CH3:13])=[N:10][C:9]([O:14][CH3:15])=[CH:8][C:3]=2[C:4]([O:6][CH3:7])=[O:5])(=[O:26])=[O:25])=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 21251118HCID 21251118, compound

Product 1

HCID 21251115Methyl 3-(4-methoxy-benzenesulfonylamino)-2,6-dimethoxy-isonicotinateYield 89%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of the product of Example 29 (0.278 g, 1.31 mmol) in pyridine (2 mL) was added p-methoxybenzenesulfonyl chloride (0.28 g, 1.38 mmol). The reaction mixture was stirred at room temperature overnight and was then quenched with H2O. The mixture was extracted 3 times with ether. The organics were combined, washed with brine, dried over MgSO4, concentrated in vacuo to provide 0.444 g (89%) of methyl 3-(4-methoxy-benzenesulfonylamino)-2,6-dimethoxy-isonicotinate as a solid. Electrospray Mass Spec: 382.8 (M+H)+

Workup

  1. customwas then quenched with H2O
  2. extractionThe mixture was extracted 3 times with ether
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e4c3cab9d3294aeda30c95fbfa4e8e8c
Source dataset
uspto-grants-2000_12
Patent number
US06162814

Reaction notes

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